Organic molecules, in particular for use in optoelectronic devices

ABSTRACT

The invention relates to an organic molecule, in particular for use in optoelectronic devices. According to the invention, the organic molecule consists of
     a first chemical moiety with a structure of formula I,   

     
       
         
         
             
             
         
       
         
         and 
         two second chemical moieties, each at each occurrence independently from another with a structure of formula II, 
       
    
     
       
         
         
             
             
         
       
         
         wherein the first chemical moiety is linked to each of the two second chemical moieties via a single bond; 
         wherein 
         T, V is independently from another the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is hydrogen; 
         W, X, Y is independently from another the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is selected from the group consisting of hydrogen, CN and CF 3 ; 
         wherein exactly one substituent selected of the group consisting of W, X, and Y is CN or CF 3 , 
         and exactly two substituents selected of the group consisting of T, V, W, X and Y represent the binding sites of a single bond linking the first chemical moiety to one of the two second chemical moieties.

The invention relates to organic molecules and their use in organiclight-emitting diodes (OLEDs) and in other optoelectronic devices.

DESCRIPTION

The object of the present invention is to provide molecules which aresuitable for use in optoelectronic devices.

This object is achieved by the invention which provides a new class oforganic molecules.

According to the invention, the organic molecules are purely organicmolecules, i.e. they do not contain any metal ions in contrast to metalcomplexes known for use in optoelectronic devices.

According to the present invention, the organic molecules exhibitemission maxima in the blue, sky-blue or green spectral range. Theorganic molecules exhibit in particular emission maxima between 420 nmand 520 nm, preferably between 440 nm and 495 nm, more preferablybetween 450 nm and 470 nm. The photoluminescence quantum yields of theorganic molecules according to the invention are, in particular, 70% ormore. The molecules according to the invention exhibit in particularthermally activated delayed fluorescence (TADF). The use of themolecules according to the invention in an optoelectronic device, forexample an organic light-emitting diode (OLED), leads to higherefficiencies of the device. Corresponding OLEDs have a higher stabilitythan OLEDs with known emitter materials and comparable color.

The organic molecules according to the invention comprise or consist ofa first chemical moiety comprising or consisting of a structure ofFormula I,

and

two second chemical moieties, each independently from another comprisingor consisting of a structure of Formula II,

wherein the first chemical moiety is linked to each of the two secondchemical moieties via a single bond.

T is the binding site of a single bond linking the first chemical moietyto one of the two second chemical moieties, or is hydrogen.

V is the binding site of a single bond linking the first chemical moietyto one of the two second chemical moieties, or is hydrogen.

W is the binding site of a single bond linking the first chemical moietyto one of the two second chemical moieties, or is selected from thegroup consisting of hydrogen, CN and CF₃.

X is the binding site of a single bond linking the first chemical moietyto one of the two second chemical moieties or is selected from the groupconsisting of hydrogen, CN and CF₃.

Y is the binding site of a single bond linking the first chemical moietyto one of the two second chemical moieties or is selected from the groupconsisting of hydrogen, CN and CF₃.

# represents the binding site of a single bond linking the firstchemical moiety to one of the two second chemical moieties.

Z is at each occurrence independently from another selected from thegroup consisting of a direct bond, CR³R⁴, C═CR³R⁴, C═O, C═NR³, NR³, O,SiR³R⁴, S, S(O) and S(O)₂.

R¹ is at each occurrence independently from another selected from thegroup consisting of hydrogen,

deuterium,

C₁-C₅-alkenyl,

-   -   wherein one or more hydrogen atoms are optionally substituted by        deuterium;

C₂-C₈-alkenyl,

-   -   wherein one or more hydrogen atoms are optionally substituted by        deuterium;

C₂-C₈-alkynyl,

-   -   wherein one or more hydrogen atoms are optionally substituted by        deuterium; and

C₆-C₁₈-aryl,

-   -   which is optionally substituted with one or more substituents        R⁶.

R² is at each occurrence independently from another selected from thegroup consisting of hydrogen,

deuterium,

C₁-C₅-alkyl,

-   -   wherein one or more hydrogen atoms are optionally substituted by        deuterium;

C₂-C₈-alkenyl,

-   -   wherein one or more hydrogen atoms are optionally substituted by        deuterium;

C₂-C₈-alkenyl,

-   -   wherein one or more hydrogen atoms are optionally substituted by        deuterium; and

C₆-C₁₈-aryl,

-   -   which is optionally substituted with one or more substituents        R⁶.

R^(m) is at each occurrence independently from another selected from thegroup consisting of hydrogen,

deuterium,

C₁-C₅-alkyl,

-   -   wherein one or more hydrogen atoms are optionally substituted by        deuterium;

C₂-C₈-alkenyl,

-   -   wherein one or more hydrogen atoms are optionally substituted by        deuterium;

C₂-C₈-alkenyl,

-   -   wherein one or more hydrogen atoms are optionally substituted by        deuterium; and

C₆-C₁₈-aryl,

-   -   which is optionally substituted with one or more substituents        R⁶.

R^(a), R³ and R⁴ is at each occurrence independently from anotherselected from the group consisting of hydrogen,

deuterium,

N(R⁵)₂,

OR⁵,

Si(R⁵)₃,

B(OR⁵)₂,

OSO₂R⁵,

CF₃,

CN,

F,

Br,

I,

C₁-C₄₀-alkyl,

-   -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;

C₁-C₄₀-alkoxy,

-   -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;

C₁-C₄₀-thioalkoxy,

-   -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;

C₂-C₄₀-alkenyl,

-   -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;

C₂-C₄₀-alkynyl,

-   -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;

C₆-C₆₀-aryl,

-   -   which is optionally substituted with one or more substituents        R⁵; and

C₃-C₅₇-heteroaryl,

-   -   which is optionally substituted with one or more substituents        R⁵.

R⁵ is at each occurrence independently from another selected from thegroup consisting of hydrogen,

deuterium,

N(R⁶)₂,

OR⁶,

Si(R⁶)₃,

B(OR⁶)₂,

OSO₂R⁶,

CF₃,

CN,

F,

Br,

I,

C₁-C₄₀-alkyl,

-   -   which is optionally substituted with one or more substituents R⁶        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,        C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;

C₁-C₄₀-alkoxy,

-   -   which is optionally substituted with one or more substituents R⁶        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,        C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;

C₁-C₄₀-thioalkoxy,

-   -   which is optionally substituted with one or more substituents R⁶        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,        C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;

C₂-C₄₀-alkenyl,

-   -   which is optionally substituted with one or more substituents R⁶        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,        C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;

C₂-C₄₀-alkynyl,

-   -   which is optionally substituted with one or more substituents R⁶        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,        C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;

C₆-C₆₀-aryl,

-   -   which is optionally substituted with one or more substituents        R⁶; and

C₃-C₅₇-heteroaryl,

-   -   which is optionally substituted with one or more substituents        R⁶.

R⁶ is at each occurrence independently from another selected from thegroup consisting of hydrogen,

deuterium,

OPh,

CF₃,

CN,

F,

C₁-C₅-alkyl,

-   -   wherein optionally one or more hydrogen atoms are independently        from each other substituted by deuterium, CN, CF₃, or F;

C₁-C₅-alkoxy,

-   -   wherein optionally one or more hydrogen atoms are independently        from each other substituted by deuterium, CN, CF₃, or F;

C₁-C₅-thioalkoxy,

-   -   wherein optionally one or more hydrogen atoms are independently        from each other substituted by deuterium, CN, CF₃, or F;

C₂-C₅-alkenyl,

-   -   wherein optionally one or more hydrogen atoms are independently        from each other substituted by deuterium, CN, CF₃, or F;

C₂-C₅-alkynyl,

-   -   wherein optionally one or more hydrogen atoms are independently        from each other substituted by deuterium, CN, CF₃, or F;

C₆-C₁₈-aryl,

-   -   which is optionally substituted with one or more C₁-C₅-alkyl        substituents;

C₃-C₁₇-heteroaryl,

-   -   which is optionally substituted with one or more C₁-C₅-alkyl        substituents;

N(C₆-C₁₈-aryl)₂;

N(C₃-C₁₇-heteroaryl)₂; and

N(C₃-C₁₇-heteroaryl)(C₆-C₁₈-aryl).

The substituents R^(a), R³, R⁴ or R⁵ independently from each other canoptionally form a mono- or polycyclic, aliphatic, aromatic and/orbenzo-fused ring system with one or more substituents R^(a), R³, R⁴ orR⁵.

According to the invention exactly one substituent selected from thegroup consisting of W, X, and Y is CN or CF₃, and exactly twosubstituents selected from the group consisting of T, V, W, X and Yrepresent the binding site of a single bond linking the first chemicalmoiety and one of the two second chemical moieties.

In one embodiment, R¹, R² and R^(m) is at each occurrence independentlyfrom another selected from the group consisting of H, methyl and phenyl.

In one embodiment, W is the binding site of a single bond linking thefirst chemical moiety to one of the two second chemical moieties, or isselected from the group consisting of CN and CF₃.

In one embodiment of the invention, W is CN.

In a further embodiment of the invention, the two second chemicalmoieties each at each occurrence independently from another comprise orconsist of a structure of Formula IIa:

wherein # and R^(a) are defined as above.

In a further embodiment of the invention, R^(a) is at each occurrenceindependently from another selected from the group consisting of H,

Me,

^(i)Pr,

^(t)Bu,

CN,

CF₃,

-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyridinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyrimidinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   carbazolyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph, and N(Ph)₂.

In a further embodiment of the invention, R^(a) is at each occurrenceindependently from another selected from the group consisting of H,

Me,

^(i)Pr,

^(t)Bu,

CN,

CF₃,

-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyridinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyrimidinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph, and-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph.

In a further embodiment of the invention, R^(a) is at each occurrenceindependently from another selected from the group consisting of H,

Me,

^(t)Bu,

-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph.

In a further embodiment of the invention, R^(a) is H at each occurrence.

In a further embodiment of the invention, the two second chemicalmoieties each at each occurrence independently from another comprise orconsist of a structure of Formula IIb, a structure of Formula IIb-2, astructure of Formula IIb-3 or a structure of Formula IIb-4:

wherein

R^(b) is at each occurrence independently from another selected from thegroup consisting of hydrogen,

deuterium,

N(R⁵)₂,

OR⁵,

Si(R⁵)₃,

B(OR⁵)₂,

OSO₂R⁵,

CF₃,

CN,

F,

Br,

I,

C₁-C₄₀-alkyl,

-   -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;

C₁-C₄₀-alkoxy,

-   -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;

C₁-C₄₀-thioalkoxy,

-   -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;

C₂-C₄₀-alkenyl,

-   -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C═C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;

C₂-C₄₀-alkynyl,

-   -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C═C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;

C₆-C₆₀-aryl,

-   -   which is optionally substituted with one or more substituents        R⁵; and

C₃-C₅₇-heteroaryl,

-   -   which is optionally substituted with one or more substituents        R⁵.

Apart from that the aforementioned definitions apply.

In one additional embodiment of the invention, the two second chemicalmoieties each at each occurrence independently from another comprise orconsist of a structure of Formula IIc, a structure of Formula IIc-2, astructure of Formula IIc-3 or a structure of Formula IIc-4:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, R^(b) is at each occurrenceindependently from another selected from the group consisting of

Me,

^(i)Pr,

^(t)Bu,

CN,

CF₃,

-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyridinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyrimidinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   carbazolyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph, and N(Ph)₂.

In a further embodiment of the invention, R^(b) is at each occurrenceindependently from another selected from the group consisting of

Me,

^(i)Pr,

^(t)Bu,

CN,

CF₃,

-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyridinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyrimidinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph, and-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph.

In a further embodiment of the invention, R^(b) is at each occurrenceindependently from another selected from the group consisting of

Me,

^(t)Bu,

-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph.

In the following, exemplary embodiments of the second chemical moietyare shown:

wherein for #, Z, R^(a), R³, R⁴ and R⁵ the aforementioned definitionsapply.

In one embodiment, R^(a) and R⁵ is at each occurrence independently fromanother selected from the group consisting of hydrogen (H), methyl (Me),i-propyl (CH(CH₃)₂) (^(i)Pr), t-butyl (^(t)Bu), phenyl (Ph), CN, CF₃,and diphenylamine (NPh₂).

In one embodiment of the invention, the organic molecules comprise orconsist of a structure of Formula III-1 or Formula III-2.

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula IIIa-1 or Formula IIIa-2:

wherein

R^(c) is at each occurrence independently from another selected from thegroup consisting of

Me,

^(i)Pr,

^(t)Bu,

-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyridinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyrimidinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   carbazolyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph, and N(Ph)₂.

In one additional embodiment of the invention, the organic moleculescomprise or consist of a structure of Formula IIIb-1 or Formula IIIb-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula IIIc-1 or Formula IIIc-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula IIId-1 or Formula IIId-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula IIIe-1 or Formula IIIe-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula IIIf-1 or Formula IIIf-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula IIIg-1 or Formula IIIg-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula IIIh-1 or Formula IIIh-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula IV-1 or Formula IV-2:

wherein the aforementioned definitions.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula IVa-1 or Formula IVa-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula IVb-1 or Formula IVb-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula IVc-1 or Formula IVc-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula IVd-1 or Formula IVd-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula IVe-1 or Formula IVe-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula IVf-1 or Formula IVf-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula IVg-1 or Formula IVg-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula IVh-1 or Formula IVh-2:

wherein the aforementioned definitions apply.

In one embodiment of the invention, the organic molecules comprise orconsist of a structure of Formula V-1 or Formula V-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula Va-1 or Formula Va-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula Vb-1 or Formula Vb-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula Vc-1 or Formula Vc-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula Vd-1 or Formula Vd-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula Ve-1 or Formula Ve-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula Vf-1 or Formula Vf-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula Vg-1 or Formula Vg-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula Vh-1 or Formula Vh-2:

wherein the aforementioned definitions apply.

In one embodiment of the invention, the organic molecules comprise orconsist of a structure of Formula VI-1 or Formula VI-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIa-1 or Formula VIa-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIb-1 or Formula VIb-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIc-1 or Formula VIc-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VId-1 or Formula VId-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIe-1 or Formula VIe-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIf-1 or Formula VIf-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIg-1 or Formula VIg-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIh-1 or Formula VIh-2:

wherein the aforementioned definitions apply.

In one embodiment of the invention, the organic molecules comprise orconsist of a structure of Formula VII-1 or Formula VII-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIIa-1 or Formula VIIa-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIIb-1 Formula VIIb-2.

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIIc-1 or Formula VIIc-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIId-1 or Formula VIId-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIIe-1 or Formula VIIe-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIIf-1 or Formula VIIf-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIIg-1 or Formula VIIg-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIIh-1 or Formula VIIh-2:

wherein the aforementioned definitions apply.

In one embodiment of the invention, the organic molecules comprise orconsist of a structure of Formula VIII-1 or Formula VIII-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIIIa-1 or Formula VIIIa-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIIIb-1 or Formula VIIIb-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIIIc-1 or Formula VIIIc-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIIId-1 or Formula VIIId-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIIIe-1 or Formula VIIIe-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIIIf-1 or Formula VIIIf-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIIIg-1 or Formula VIIIg-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure of Formula VIIIh-1 or Formula VIIIh-2:

wherein the aforementioned definitions apply.

In one embodiment of the invention, R^(c) is at each occurrenceindependently from another selected from the group consisting of

Me,

^(i)Pr,

^(t)Bu,

CN,

CF₃,

-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyridinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyrimidinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph, and-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph.

In one embodiment of the invention R^(c) is at each occurrenceindependently from another selected from the group consisting of

Me,

^(t)Bu,

-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃ and Ph; and-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃ and Ph.

As used throughout the present application, the terms “aryl” and“aromatic” may be understood in the broadest sense as any mono-, bi- orpolycyclic aromatic moieties. Accordingly, an aryl group contains 6 to60 aromatic ring atoms, and a heteroaryl group contains 5 to 60 aromaticring atoms, of which at least one is a heteroatom. Notwithstanding,throughout the application the number of aromatic ring atoms may begiven as subscripted number in the definition of certain substituents.In particular, the heteroaromatic ring includes one to threeheteroatoms. Again, the terms “heteroaryl” and “heteroaromatic” may beunderstood in the broadest sense as any mono-, bi- or polycyclichetero-aromatic moieties that include at least one heteroatom. Theheteroatoms may at each occurrence be the same or different and beindividually selected from the group consisting of N, O and S.Accordingly, the term “arylene” refers to a divalent substituent thatbears two binding sites to other molecular structures and therebyserving as a linker structure. In case, a group in the exemplaryembodiments is defined differently from the definitions given here, forexample, the number of aromatic ring atoms or number of heteroatomsdiffers from the given definition, the definition in the exemplaryembodiments is to be applied. According to the invention, a condensed(annulated) aromatic or heteroaromatic polycycle is built of two or moresingle aromatic or heteroaromatic cycles, which formed the polycycle viaa condensation reaction.

In particular, as used throughout the present application the term arylgroup or heteroaryl group comprises groups which can be bound via anyposition of the aromatic or heteroaromatic group, derived from benzene,naphthaline, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene,perylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene,pentacene, benzpyrene, furan, benzofuran, isobenzofuran, dibenzofuran,thiophene, benzothiophene, isobenzothiophene, dibenzothiophene; pyrrole,indole, isoindole, carbazole, pyridine, quinoline, isoquinoline,acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline,benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole,imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole,pyridoimidazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole,benzoxazole, napthooxazole, anthroxazol, phenanthroxazol, isoxazole,1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine,pyrimidine, benzopyrimidine, 1,3,5-triazine, quinoxaline, pyrazine,phenazine, naphthyridine, carboline, benzocarboline, phenanthroline,1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole,1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,2,3,4-tetrazine, purine,pteridine, indolizine and benzothiadiazole or combinations of theabovementioned groups.

As used throughout the present application the term cyclic group may beunderstood in the broadest sense as any mono-, bi- or polycyclicmoieties.

As used throughout the present application the term alkyl group may beunderstood in the broadest sense as any linear, branched, or cyclicalkyl substituent. In particular, the term alkyl comprises thesubstituents methyl (Me), ethyl (Et), n-propyl (^(n)Pr), i-propyl (¹Pr),cyclopropyl, n-butyl (^(n)Bu), i-butyl (^(i)Bu), s-butyl (^(s)Bu),t-butyl (^(t)Bu), cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl,t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl,2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl,2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl,1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl,1-bicyclo[2,2,2]octyl, 2-bicyclo[2,2,2]-octyl, 2-(2,6-dimethyl)octyl,3-(3,7-dimethyl)octyl, adamantyl, 2,2,2-trifluorethyl,1,1-dimethyl-n-hex-1-yl, 1,1-dimethyl-n-hept-1-yl,1,1-dimethyl-n-oct-1-yl, 1,1-dimethyl-n-dec-1-yl,1,1-dimethyl-n-dodec-1-yl, 1,1-dimethyl-n-tetradec-1-yl,1,1-dimethyl-n-hexadec-1-yl, 1, 1-dimethyl-n-octadec-1-yl, 1,1-diethyl-n-hex-1-yl, 1, 1-diethyl-n-hept-1-yl, 1, 1-diethyl-n-oct-1-yl,1,1-diethyl-n-dec-1-yl, 1,1-diethyl-n-dodec-1-yl,1,1-diethyl-n-tetradec-1-yl, 1,1-diethyln-n-hexadec-1-yl,1,1-diethyl-n-octadec-1-yl, 1-(n-propyl)-cyclohex-1-yl,1-(n-butyl)-cyclohex-1-yl, 1-(n-hexyl)-cyclohex-1-yl,1-(n-octyl)-cyclohex-1-yl and 1-(n-decyl)-cyclohex-1-yl.

As used throughout the present application the term alkenyl compriseslinear, branched, and cyclic alkenyl substituents. The term alkenylgroup exemplarily comprises the substituents ethenyl, propenyl, butenyl,pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl,octenyl, cyclooctenyl or cyclooctadienyl.

As used throughout the present application the term alkynyl compriseslinear, branched, and cyclic alkynyl substituents. The term alkynylgroup exemplarily comprises ethynyl, propynyl, butynyl, pentynyl,hexynyl, heptynyl or octynyl.

As used throughout the present application the term alkoxy compriseslinear, branched, and cyclic alkoxy substituents. The term alkoxy groupexemplarily comprises methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy,i-butoxy, s-butoxy, t-butoxy and 2-methylbutoxy.

As used throughout the present application the term thioalkoxy compriseslinear, branched, and cyclic thioalkoxy substituents, in which the O ofthe exemplarily alkoxy groups is replaced by S.

As used throughout the present application, the terms “halogen” and“halo” may be understood in the broadest sense as being preferablyfluorine, chlorine, bromine or iodine.

Whenever hydrogen is mentioned herein, it could also be replaced bydeuterium at each occurrence.

It is understood that when a molecular fragment is described as being asubstituent or otherwise attached to another moiety, its name may bewritten as if it were a fragment (e.g. naphtyl, dibenzofuryl) or as ifit were the whole molecule (e.g. naphthalene, dibenzofuran). As usedherein, these different ways of designating a substituent or attachedfragment are considered to be equivalent.

In one embodiment, the organic molecules according to the invention havean excited state lifetime of not more than 150 μs, of not more than 100μs, in particular of not more than 50 μs, more preferably of not morethan 10 μs or not more than 7 μs in a film of poly(methyl methacrylate)(PMMA) with 10% by weight of organic molecule at room temperature.

In one embodiment of the invention, the organic molecules according tothe invention represent thermally-activated delayed fluorescence (TADF)emitters, which exhibit a ΔE_(ST) value, which corresponds to the energydifference between the first excited singlet state (S1) and the firstexcited triplet state (T1), of less than 5000 cm⁻¹, preferably less than3000 cm⁻¹, more preferably less than 1500 cm⁻¹, even more preferablyless than 1000 cm⁻¹ or even less than 500 cm⁻¹.

In a further embodiment of the invention, the organic moleculesaccording to the invention have an emission peak in the visible ornearest ultraviolet range, i.e., in the range of a wavelength of from380 to 800 nm, with a full width at half maximum of less than 0.50 eV,preferably less than 0.48 eV, more preferably less than 0.45 eV, evenmore preferably less than 0.43 eV or even less than 0.40 eV in a film ofpoly(methyl methacrylate) (PMMA) with 10% by weight of organic moleculeat room temperature.

In a further embodiment of the invention, the organic moleculesaccording to the invention have a “blue material index” (BMI),calculated by dividing the photoluminescence quantum yield (PLQY) in %by the CIEy color coordinate of the emitted light, of more than 150, inparticular more than 200, preferably more than 250, more preferably ofmore than 300 or even more than 500.

Orbital and excited state energies can be determined either by means ofexperimental methods or by calculations employing quantum-chemicalmethods, in particular density functional theory calculations. Theenergy of the highest occupied molecular orbital E^(HOMO) is determinedby methods known to the person skilled in the art from cyclicvoltammetry measurements with an accuracy of 0.1 eV. The energy of thelowest unoccupied molecular orbital E^(LUMO) is calculated asE^(HOMO)+E^(gap), wherein E^(gap) is determined as follows: For hostcompounds, the onset of the emission spectrum of a film with 10% byweight of host in poly(methyl methacrylate) (PMMA) is used as E^(gap),unless stated otherwise. For emitter molecules, E^(gap) is determined asthe energy at which the excitation and emission spectra of a film with10% by weight of emitter in PMMA cross.

The energy of the first excited triplet state T1 is determined from theonset of the emission spectrum at low temperature, typically at 77 K.For host compounds, where the first excited singlet state and the lowesttriplet state are energetically separated by >0.4 eV, thephosphorescence is usually visible in a steady-state spectrum in2-Me-THF. The triplet energy can thus be determined as the onset of thephosphorescence spectrum. For TADF emitter molecules, the energy of thefirst excited triplet state T1 is determined from the onset of thedelayed emission spectrum at 77 K, if not otherwise stated measured in afilm of) PMMA with 10% by weight of emitter. Both for host and emittercompounds, the energy of the first excited singlet state S1 isdetermined from the onset of the emission spectrum, if not otherwisestated measured in a film of PMMA with 10% by weight of host or emittercompound. The onset of an emission spectrum is determined by computingthe intersection of the tangent to the emission spectrum with thex-axis. The tangent to the emission spectrum is set at the high-energyside of the emission band, i.e., where the emission band rises by goingfrom higher energy values to lower energy values, and at the point athalf maximum of the maximum intensity of the emission spectrum.

A further aspect of the invention relates to a process for preparingorganic molecules (with an optional subsequent reaction) according tothe invention, wherein a2-Trifluormethyl-3-R¹-5-R¹-4-R²-6-R^(m)-phenylboronic acid is used as areactant:

According to the invention, in the reaction for the synthesis of E1 aboronic acid ester can be used instead of a boronic acid.

For the reaction of a nitrogen heterocycle in a nucleophilic aromaticsubstitution with an aryl halide, preferably an aryl fluoride, typicalconditions include the use of a base, such as tribasic potassiumphosphate or sodium hydride, for example, in an aprotic polar solvent,such as dimethyl sulfoxide (DMSO) or N,N-dimethylformamide (DMF), forexample.

An alternative synthesis route comprises the introduction of a nitrogenheterocycle via copper- or palladium-catalyzed coupling to an arylhalide or aryl pseudohalide, preferably an aryl bromide, an aryl iodide,aryl triflate or an aryl tosylate.

A further aspect of the invention relates to the use of an organicmolecule according to the invention as a luminescent emitter or as anabsorber, and/or as host material and/or as electron transport material,and/or as hole injection material, and/or as hole blocking material inan optoelectronic device.

The organic electroluminescent device may be understood in the broadestsense as any device based on organic materials that is suitable foremitting light in the visible or nearest ultraviolet (UV) range, i.e.,in the range of a wavelength of from 380 to 800 nm. More preferably,organic electroluminescent device may be able to emit light in thevisible range, i.e., of from 400 to 800 nm.

In the context of such use, the optoelectronic device is moreparticularly selected from the group consisting of:

-   -   organic light-emitting diodes (OLEDs),    -   light-emitting electrochemical cells,    -   OLED sensors, especially in gas and vapour sensors not        hermetically externally shielded,    -   organic diodes,    -   organic solar cells,    -   organic transistors,    -   organic field-effect transistors,    -   organic lasers and    -   down-conversion elements.

In a preferred embodiment in the context of such use, the organicelectroluminescent device is a device selected from the group consistingof an organic light emitting diode (OLED), a light emittingelectrochemical cell (LEC), and a light-emitting transistor.

In the case of the use, the fraction of the organic molecule accordingto the invention in the emission layer in an optoelectronic device, moreparticularly in OLEDs, is 1% to 99% by weight, more particularly 5% to80% by weight. In an alternative embodiment, the proportion of theorganic molecule in the emission layer is 100% by weight.

In one embodiment, the light-emitting layer comprises not only theorganic molecules according to the invention but also a host materialwhose triplet (T1) and singlet (S1) energy levels are energeticallyhigher than the triplet (T1) and singlet (S1) energy levels of theorganic molecule.

A further aspect of the invention relates to a composition comprising orconsisting of:

-   (a) at least one organic molecule according to the invention, in    particular in the form of an emitter and/or a host, and-   (b) one or more emitter and/or host materials, which differ from the    organic molecule according to the invention and-   (c) optional one or more dyes and/or one or more solvents.

In one embodiment, the light-emitting layer comprises (or (essentially)consists of) a composition comprising or consisting of:

-   (a) at least one organic molecule according to the invention, in    particular in the form of an emitter and/or a host, and-   (b) one or more emitter and/or host materials, which differ from the    organic molecule according to the invention and-   (c) optional one or more dyes and/or one or more solvents.

Particularly preferably the light-emitting layer EML comprises (or(essentially) consists of) a composition comprising or consisting of:

-   (i) 1-50% by weight, preferably 5-40% by weight, in particular    10-30% by weight, of one or more organic molecules according to the    invention;-   (ii) 5-99% by weight, preferably 30-94.9% by weight, in particular    40-89% by weight, of at least one host compound H; and-   (iii) optionally 0-94% by weight, preferably 0.1-65% by weight, in    particular 1-50% by weight, of at least one further host compound D    with a structure differing from the structure of the molecules    according to the invention; and-   (iv) optionally 0-94% by weight, preferably 0-65% by weight, in    particular 0-50% by weight, of a solvent; and-   (v) optionally 0-30% by weight, in particular 0-20% by weight,    preferably 0-5% by weight, of at least one further emitter molecule    F with a structure differing from the structure of the molecules    according to the invention.

Preferably, energy can be transferred from the host compound H to theone or more organic molecules according to the invention, in particulartransferred from the first excited triplet state T1(H) of the hostcompound H to the first excited triplet state T1(E) of the one or moreorganic molecules according to the invention and/or from the firstexcited singlet state S1(H) of the host compound H to the first excitedsinglet state S1(E) of the one or more organic molecules according tothe invention.

In a further embodiment, the light-emitting layer EML comprises (or(essentially) consists of) a composition comprising or consisting of:

-   (i) 1-50% by weight, preferably 5-40% by weight, in particular    10-30% by weight, of one organic molecule according to the    invention;-   (ii) 5-99% by weight, preferably 30-94.9% by weight, in particular    40-89% by weight, of one host compound H; and-   (iii) optionally 0-94% by weight, preferably 0.1-65% by weight, in    particular 1-50% by weight, of at least one further host compound D    with a structure differing from the structure of the molecules    according to the invention; and-   (iv) optionally 0-94% by weight, preferably 0-65% by weight, in    particular 0-50% by weight, of a solvent; and-   (v) optionally 0-30% by weight, in particular 0-20% by weight,    preferably 0-5% by weight, of at least one further emitter molecule    F with a structure differing from the structure of the molecules    according to the invention.

In one embodiment, the host compound H has a highest occupied molecularorbital HOMO(H) having an energy E^(HOMO)(H) in the range of from −5 to−6.5 eV and the at least one further host compound D has a highestoccupied molecular orbital HOMO(D) having an energy E^(HOMO)(D), whereinE^(HOMO)(H)>E^(HOMO)(D).

In a further embodiment, the host compound H has a lowest unoccupiedmolecular orbital LUMO(H) having an energy E^(LUMO)(H) and the at leastone further host compound D has a lowest unoccupied molecular orbitalLUMO(D) having an energy E^(LUMO)(D), wherein E^(LUMO)(H)>E^(LUMO)(D).

In one embodiment, the host compound H has a highest occupied molecularorbital HOMO(H) having an energy E^(HOMO)(H) and a lowest unoccupiedmolecular orbital LUMO(H) having an energy E^(LUMO)(H), and

-   -   the at least one further host compound D has a highest occupied        molecular orbital HOMO(D) having an energy E^(HOMO)(D) and a        lowest unoccupied molecular orbital LUMO(D) having an energy        E^(LUMO)(D),    -   the organic molecule according to the invention has a highest        occupied molecular orbital HOMO(E) having an energy E^(HOMO)(E)        and a lowest unoccupied molecular orbital LUMO(E) having an        energy E^(LUMO)(E),

wherein

E^(HOMO)(H)>E^(HOMO)(D) and the difference between the energy level ofthe highest occupied molecular orbital HOMO(E) of organic moleculeaccording to the invention (E^(HOMO)(E)) and the energy level of thehighest occupied molecular orbital HOMO(H) of the host compound H(E^(HOMO)(H)) is between −0.5 eV and 0.5 eV, more preferably between−0.3 eV and 0.3 eV, even more preferably between −0.2 eV and 0.2 eV oreven between −0.1 eV and 0.1 eV; and E^(LUMO)(H)>E^(LUMO)(D) and thedifference between the energy level of the lowest unoccupied molecularorbital LUMO(E) of organic molecule according to the invention(E^(LUMO)(E)) and the lowest unoccupied molecular orbital LUMO(D) of theat least one further host compound D (E^(LUMO)(D)) is between −0.5 eVand 0.5 eV, more preferably between −0.3 eV and 0.3 eV, even morepreferably between −0.2 eV and 0.2 eV or even between −0.1 eV and 0.1eV.

In a further aspect, the invention relates to an optoelectronic devicecomprising an organic molecule or a composition of the type describedhere, more particularly in the form of a device selected from the groupconsisting of organic light-emitting diode (OLED), light-emittingelectrochemical cell, OLED sensor, more particularly gas and vapoursensors not hermetically externally shielded, organic diode, organicsolar cell, organic transistor, organic field-effect transistor, organiclaser and down-conversion element.

In a preferred embodiment, the organic electroluminescent device is adevice selected from the group consisting of an organic light emittingdiode (OLED), a light emitting electrochemical cell (LEC), and alight-emitting transistor.

In one embodiment of the optoelectronic device of the invention, theorganic molecule according to the invention is used as emission materialin a light-emitting layer EML.

In one embodiment of the optoelectronic device of the invention thelight-emitting layer EML consists of the composition according to theinvention described here.

Exemplarily, when the organic electroluminescent device is an OLED, itmay exhibit the following layer structure:

-   1. substrate-   2. anode layer A-   3. hole injection layer, HIL-   4. hole transport layer, HTL-   5. electron blocking layer, EBL-   6. emitting layer, EML-   7. hole blocking layer, HBL-   8. electron transport layer, ETL-   9. electron injection layer, EIL-   10. cathode layer,

wherein the OLED comprises each layer only optionally, different layersmay be merged and the OLED may comprise more than one layer of eachlayer type defined above.

Furthermore, the organic electroluminescent device may optionallycomprise one or more protective layers protecting the device fromdamaging exposure to harmful species in the environment including,exemplarily moisture, vapor and/or gases.

In one embodiment of the invention, the organic electroluminescentdevice is an OLED, which exhibits the following inverted layerstructure:

-   1. substrate-   2. cathode layer-   3. electron injection layer, EIL-   4. electron transport layer, ETL-   5. hole blocking layer, HBL-   6. emitting layer, B-   7. electron blocking layer, EBL-   8. hole transport layer, HTL-   9. hole injection layer, HIL-   10. anode layer A

Wherein the OLED with an inverted layer structure comprises each layeronly optionally, different layers may be merged and the OLED maycomprise more than one layer of each layer types defined above.

In one embodiment of the invention, the organic electroluminescentdevice is an OLED, which may exhibit stacked architecture. In thisarchitecture, contrary to the typical arrangement, where the OLEDs areplaced side by side, the individual units are stacked on top of eachother. Blended light may be generated with OLEDs exhibiting a stackedarchitecture, in particular white light may be generated by stackingblue, green and red OLEDs. Furthermore, the OLED exhibiting a stackedarchitecture may optionally comprise a charge generation layer (CGL),which is typically located between two OLED subunits and typicallyconsists of a n-doped and p-doped layer with the n-doped layer of oneCGL being typically located closer to the anode layer.

In one embodiment of the invention, the organic electroluminescentdevice is an OLED, which comprises two or more emission layers betweenanode and cathode. In particular, this so-called tandem OLED comprisesthree emission layers, wherein one emission layer emits red light, oneemission layer emits green light and one emission layer emits bluelight, and optionally may comprise further layers such as chargegeneration layers, blocking or transporting layers between theindividual emission layers. In a further embodiment, the emission layersare adjacently stacked. In a further embodiment, the tandem OLEDcomprises a charge generation layer between each two emission layers. Inaddition, adjacent emission layers or emission layers separated by acharge generation layer may be merged.

The substrate may be formed by any material or composition of materials.Most frequently, glass slides are used as substrates. Alternatively,thin metal layers (e.g., copper, gold, silver or aluminum films) orplastic films or slides may be used. This may allow a higher degree offlexibility. The anode layer A is mostly composed of materials allowingto obtain an (essentially) transparent film. As at least one of bothelectrodes should be (essentially) transparent in order to allow lightemission from the OLED, either the anode layer A or the cathode layer Cis transparent. Preferably, the anode layer A comprises a large contentor even consists of transparent conductive oxides (TCOs). Such anodelayer A may exemplarily comprise indium tin oxide, aluminum zinc oxide,fluorine doped tin oxide, indium zinc oxide, PbO, SnO, zirconium oxide,molybdenum oxide, vanadium oxide, wolfram oxide, graphite, doped Si,doped Ge, doped GaAs, doped polyaniline, doped polypyrrol and/or dopedpolythiophene.

Particularly preferably, the anode layer A (essentially) consists ofindium tin oxide (ITO) (e.g., (InO3)0.9(SnO2)0.1). The roughness of theanode layer A caused by the transparent conductive oxides (TCOs) may becompensated by using a hole injection layer (HIL). Further, the HIL mayfacilitate the injection of quasi charge carriers (i.e., holes) in thatthe transport of the quasi charge carriers from the TCO to the holetransport layer (HTL) is facilitated. The hole injection layer (HIL) maycomprise poly-3,4-ethylendioxy thiophene (PEDOT), polystyrene sulfonate(PSS), MoO₂, V₂O₅, CuPC or CuI, in particular a mixture of PEDOT andPSS. The hole injection layer (HIL) may also prevent the diffusion ofmetals from the anode layer A into the hole transport layer (HTL). TheHIL may exemplarily comprise PEDOT:PSS (poly-3,4-ethylendioxy thiophene:polystyrene sulfonate), PEDOT (poly-3,4-ethylendioxy thiophene), mMTDATA(4,4′,4″-tris[phenyl(m-tolyl)amino]triphenylamine), Spiro-TAD(2,2′,7,7′-tetrakis(n,n-diphenylamino)-9,9′-spirobifluorene), DNTPD(N1,N1′-(biphenyl-4,4′-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine),NPB(N,N′-nis-(1-naphthalenyl)-N,N′-bis-phenyl-(1,1′-biphenyl)-4,4′-diamine),NPNPB (N,N′-diphenyl-N,N′-di-[4-(N,N-diphenyl-amino)phenyl]benzidine),MeO-TPD (N,N,N′,N′-tetrakis(4-methoxyphenyl)benzidine), HAT-CN(1,4,5,8,9,11-hexaazatriphenylen-hexacarbonitrile) and/or Spiro-NPD(N,N′-diphenyl-N,N′-bis-(1-naphthyl)-9,9′-spirobifluorene-2,7-diamine).

Adjacent to the anode layer A or hole injection layer (HIL) typically ahole transport layer (HTL) is located. Herein, any hole transportcompound may be used. Exemplarily, electron-rich heteroaromaticcompounds such as triarylamines and/or carbazoles may be used as holetransport compound. The HTL may decrease the energy barrier between theanode layer A and the light-emitting layer EML. The hole transport layer(HTL) may also be an electron blocking layer (EBL). Preferably, holetransport compounds bear comparably high energy levels of their tripletstates T1. Exemplarily the hole transport layer (HTL) may comprise astar-shaped heterocycle such as tris(4-carbazoyl-9-ylphenyl)amine(TCTA), poly-TPD (poly(4-butylphenyl-diphenyl-amine)), [alpha]-NPD(poly(4-butylphenyl-diphenyl-amine)), TAPC (4,4′-cyclohexyliden-bis[N,N-bis(4-methylphenyl)benzenamine]), 2-TNATA(4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine), Spiro-TAD, DNTPD,NPB, NPNPB, MeO-TPD, HAT-CN and/or TrisPcz(9,9′-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9′H-3,3′-bicarbazole).In addition, the HTL may comprise a p-doped layer, which may be composedof an inorganic or organic dopant in an organic hole-transportingmatrix. Transition metal oxides such as vanadium oxide, molybdenum oxideor tungsten oxide may exemplarily be used as inorganic dopant.Tetrafluorotetracyanoquinodimethane (F4-TCNQ),copper-pentafluorobenzoate (Cu(I)pFBz) or transition metal complexes mayexemplarily be used as organic dopant.

The EBL may exemplarily comprise mCP (1,3-bis(carbazol-9-yl)benzene),TCTA, 2-TNATA, mCBP (3,3-di(9H-carbazol-9-yl)biphenyl), tris-Pcz, CzSi(9-(4-tert-Butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), and/orDCB (N,N′-dicarbazolyl-1,4-dimethylbenzene).

Adjacent to the hole transport layer (HTL), typically, thelight-emitting layer EML is located. The light-emitting layer EMLcomprises at least one light emitting molecule. Particular, the EMLcomprises at least one light emitting molecule according to theinvention. In one embodiment, the light-emitting layer comprises onlythe organic molecules according to the invention. Typically, the EMLadditionally comprises one or more host material. Exemplarily, the hostmaterial is selected from CBP (4,4′-Bis-(N-carbazolyl)-biphenyl), mCP,mCBP Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), CzSi, Sif88(dibenzo[b,d]thiophen-2-yl)diphenylsilane), DPEPO(bis[2-(diphenylphosphino)phenyl]ether oxide), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole,9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole,9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, T2T(2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T(2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine) and/or TST(2,4,6-tris(9,9′-spirobifluorene-2-yl)-1,3,5-triazine). The hostmaterial typically should be selected to exhibit first triplet (T1) andfirst singlet (S1) energy levels, which are energetically higher thanthe first triplet (T1) and first singlet (S1) energy levels of theorganic molecule.

In one embodiment of the invention, the EML comprises a so-calledmixed-host system with at least one hole-dominant host and oneelectron-dominant host. In a particular embodiment, the EML comprisesexactly one light emitting molecule according to the invention and amixed-host system comprising T2T as electron-dominant host and a hostselected from CBP, mCP, mCBP,9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole,9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole as hole-dominanthost. In a further embodiment the EML comprises 50-80% by weight,preferably 60-75% by weight of a host selected from CBP, mCP, mCBP,9-[3-(dibenzofuran-2-yl) phenyl]-9H-carbazole,9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole,9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole; 10-45% by weight,preferably 15-30% by weight of T2T and 5-40% by weight, preferably10-30% by weight of light emitting molecule according to the invention.

Adjacent to the light-emitting layer EML an electron transport layer(ETL) may be located. Herein, any electron transporter may be used.Exemplarily, compounds poor of electrons such as, e.g., benzimidazoles,pyridines, triazoles, oxadiazoles (e.g., 1,3,4-oxadiazole),phosphinoxides and sulfone, may be used. An electron transporter mayalso be a star-shaped heterocycle such as1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi). The ETL maycomprise NBphen(2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3(Aluminum-tris(8-hydroxyquinoline)), TSPO1(diphenyl-4-triphenylsilylphenyl-phosphinoxide), BPyTP2(2,7-di(2,2′-bipyridin-5-yl)triphenyle), Sif87(dibenzo[b,d]thiophen-2-yltriphenylsilane), Sif88(dibenzo[b,d]thiophen-2-yl)diphenylsilane), BmPyPhB(1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene) and/or BTB(4,4′-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1′-biphenyl). Optionally,the ETL may be doped with materials such as Liq. The electron transportlayer (ETL) may also block holes or a holeblocking layer (HBL) isintroduced.

The HBL may exemplarily comprise BCP(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline=Bathocuproine), BAlq(bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum), NBphen(2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3(Aluminum-tris(8-hydroxyquinoline)), TSPO1(diphenyl-4-triphenylsilylphenyl-phosphinoxide), T2T(2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T(2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine), TST(2,4,6-tris(9,9′-spirobifluorene-2-yl)-1,3,5-triazine), and/or TCB/TCP(1,3,5-tris(N-carbazolyl)benzol/1,3,5-tris(carbazol)-9-yl) benzene).

Adjacent to the electron transport layer (ETL), a cathode layer C may belocated. Exemplarily, the cathode layer C may comprise or may consist ofa metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In,W, or Pd) or a metal alloy. For practical reasons, the cathode layer mayalso consist of (essentially) intransparent metals such as Mg, Ca or Al.Alternatively or additionally, the cathode layer C may also comprisegraphite and or carbon nanotubes (CNTs). Alternatively, the cathodelayer C may also consist of nanoscalic silver wires.

An OLED may further, optionally, comprise a protection layer between theelectron transport layer (ETL) and the cathode layer C (which may bedesignated as electron injection layer (EIL)). This layer may compriselithium fluoride, cesium fluoride, silver, Liq(8-hydroxyquinolinolatolithium), Li₂O, BaF₂, MgO and/or NaF.

Optionally, also the electron transport layer (ETL) and/or a holeblocking layer (HBL) may comprise one or more host compounds.

In order to modify the emission spectrum and/or the absorption spectrumof the light-emitting layer EML further, the light-emitting layer EMLmay further comprise one or more further emitter molecule F. Such anemitter molecule F may be any emitter molecule known in the art.Preferably such an emitter molecule F is a molecule with a structurediffering from the structure of the molecules according to theinvention. The emitter molecule F may optionally be a TADF emitter.Alternatively, the emitter molecule F may optionally be a fluorescentand/or phosphorescent emitter molecule which is able to shift theemission spectrum and/or the absorption spectrum of the light-emittinglayer EML. Exemplarily, the triplet and/or singlet excitons may betransferred from the emitter molecule according to the invention to theemitter molecule F before relaxing to the ground state S0 by emittinglight typically red-shifted in comparison to the light emitted byemitter molecule E. Optionally, the emitter molecule F may also provoketwo-photon effects (i.e., the absorption of two photons of half theenergy of the absorption maximum).

Optionally, an organic electroluminescent device (e.g., an OLED) mayexemplarily be an essentially white organic electroluminescent device.Exemplarily such white organic electroluminescent device may comprise atleast one (deep) blue emitter molecule and one or more emitter moleculesemitting green and/or red light. Then, there may also optionally beenergy transmittance between two or more molecules as described above.

As used herein, if not defined more specifically in the particularcontext, the designation of the colors of emitted and/or absorbed lightis as follows:

violet: wavelength range of >380-420 nm;

deep blue: wavelength range of >420-480 nm;

sky blue: wavelength range of >480-500 nm;

green: wavelength range of >500-560 nm;

yellow: wavelength range of >560-580 nm;

orange: wavelength range of >580-620 nm;

red: wavelength range of >620-800 nm.

With respect to emitter molecules, such colors refer to the emissionmaximum. Therefore, exemplarily, a deep blue emitter has an emissionmaximum in the range of from >420 to 480 nm, a sky blue emitter has anemission maximum in the range of from >480 to 500 nm, a green emitterhas an emission maximum in a range of from >500 to 560 nm, a red emitterhas an emission maximum in a range of from >620 to 800 nm.

A deep blue emitter may preferably have an emission maximum of below 480nm, more preferably below 470 nm, even more preferably below 465 nm oreven below 460 nm. It will typically be above 420 nm, preferably above430 nm, more preferably above 440 nm or even above 450 nm.

Accordingly, a further aspect of the present invention relates to anOLED, which exhibits an external quantum efficiency at 1000 cd/m2 ofmore than 8%, more preferably of more than 10%, more preferably of morethan 13%, even more preferably of more than 15% or even more than 20%and/or exhibits an emission maximum between 420 nm and 500 nm,preferably between 430 nm and 490 nm, more preferably between 440 nm and480 nm, even more preferably between 450 nm and 470 nm and/or exhibits aLT80 value at 500 cd/m2 of more than 100 h, preferably more than 200 h,more preferably more than 400 h, even more preferably more than 750 h oreven more than 1000 h. Accordingly, a further aspect of the presentinvention relates to an OLED, whose emission exhibits a CIEy colorcoordinate of less than 0.45, preferably less than 0.30, more preferablyless than 0.20 or even more preferably less than 0.15 or even less than0.10.

A further aspect of the present invention relates to an OLED, whichemits light at a distinct color point. According to the presentinvention, the OLED emits light with a narrow emission band (small fullwidth at half maximum (FWHM)). In one aspect, the OLED according to theinvention emits light with a FWHM of the main emission peak of less than0.50 eV, preferably less than 0.48 eV, more preferably less than 0.45eV, even more preferably less than 0.43 eV or even less than 0.40 eV.

A further aspect of the present invention relates to an OLED, whichemits light with CIEx and CIEy color coordinates close to the CIEx(=0.131) and CIEy (=0.046) color coordinates of the primary color blue(CIEx=0.131 and CIEy=0.046) as defined by ITU-R Recommendation BT.2020(Rec. 2020) and thus is suited for the use in Ultra High Definition(UHD) displays, e.g. UHD-TVs. In commercial applications, typicallytop-emitting (top-electrode is transparent) devices are used, whereastest devices as used throughout the present application representbottom-emitting devices (bottom-electrode and substrate aretransparent). The CIEy color coordinate of a blue device can be reducedby up to a factor of two, when changing from a bottom- to a top-emittingdevice, while the CIEx remains nearly unchanged (Okinaka et al. (2015),22.1: Invited Paper: New Fluorescent Blue Host Materials for AchievingLow Voltage in OLEDs, SID Symposium Digest of Technical Papers, 46;doi:10.1002/sdtp.10480). Accordingly, a further aspect of the presentinvention relates to an OLED, whose emission exhibits a CIEx colorcoordinate of between 0.02 and 0.30, preferably between 0.03 and 0.25,more preferably between 0.05 and 0.20 or even more preferably between0.08 and 0.18 or even between 0.10 and 0.15 and/or a CIEy colorcoordinate of between 0.00 and 0.45, preferably between 0.01 and 0.30,more preferably between 0.02 and 0.20 or even more preferably between0.03 and 0.15 or even between 0.04 and 0.10.

In a further aspect, the invention relates to a method for producing anoptoelectronic component. In this case an organic molecule of theinvention is used.

The organic electroluminescent device, in particular the OLED accordingto the present invention can be fabricated by any means of vapordeposition and/or liquid processing. Accordingly, at least one layer is

-   -   prepared by means of a sublimation process,    -   prepared by means of an organic vapor phase deposition process,    -   prepared by means of a carrier gas sublimation process,    -   solution processed or printed.

The methods used to fabricate the organic electroluminescent device, inparticular the OLED according to the present invention are known in theart. The different layers are individually and successively deposited ona suitable substrate by means of subsequent deposition processes. Theindividual layers may be deposited using the same or differingdeposition methods.

Vapor deposition processes exemplarily comprise thermal (co)evaporation,chemical vapor deposition and physical vapor deposition. For activematrix OLED display, an AMOLED backplane is used as substrate. Theindividual layer may be processed from solutions or dispersionsemploying adequate solvents. Solution deposition process exemplarilycomprise spin coating, dip coating and jet printing. Liquid processingmay optionally be carried out in an inert atmosphere (e.g., in anitrogen atmosphere) and the solvent may optionally be completely orpartially removed by means known in the state of the art.

EXAMPLES

General Synthesis Scheme I

General Procedure for Synthesis AAV1:

2-Trifluormethylphenylboronic acid E2 (1.10 equivalents),4-bromo/chloro-2,6-difluoro-benzonitrile/benzotrifluoride (1.00equivalents), Pd₂(dba)₃ (0.01 equivalent),2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos) (0.04equivalents) and tribasic potassium phosphate (2.50 equivalents) arestirred under nitrogen atmosphere in a toluene/water mixture (ratio of10:1, 4 mL toluene/mmol aryl bromide) at 110° C. until completion of thereaction (monitoring with GC/MS, usually finished within 2-4 h).Subsequently the reaction mixture is filtrated and the residue is washedwith dichloromethane. The filtrate is added brine, the phases areseparated and the organic layer is dried over MgSO₄, filtrated andconcentrated in vacuo. The residue is purified by short columnchromatography using dichloromethane as the eluent. Instead of a boronicacid a corresponding boronic acid ester may be used.

General Procedure for Synthesis AAV2:

The synthesis of Z2 is carried out according to AAV1, wherein2-Trifluormethylphenylboronic acid E2 reacts with3-bromo/chloro-2,6-difluoro-benzonitrile/benzotrifluoride.

General Procedure for Synthesis AAV3:

The synthesis of Z3 is carried out according to AAV1, wherein2-Trifluormethylphenylboronic acid E2 reacts with4-bromo/chloro-3,5-difluoro-benzonitrile/benzotrifluoride.

General Procedure for Synthesis AAV4:

The synthesis of Z4 is carried out according to AAV1, wherein2-Trifluormethylphenylboronic acid E2 reacts with4-bromo/chloro-2,5-difluoro-benzonitrile/benzotrifluoride.

General Procedure for Synthesis AAV5:

The synthesis of Z5 is carried out according to AAV1, wherein2-Trifluormethylphenylboronic acid E2 reacts with2-bromo/chloro-4,5-difluoro-benzonitrile/benzotrifluoride.

General Procedure for Synthesis AAV6:

The synthesis of Z6 is carried out according to AAV1, wherein2-Trifluormethylphenylboronic acid E2 reacts with5-bromo/chloro-2,3-difluoro-benzonitrile/benzotrifluoride.

General Procedure for Synthesis AAV7:

Z1, Z2, Z3, Z4, Z5 or Z6 (1 equivalent each), the corresponding donormolecule D-H (2.00 equivalents) and tribasic potassium phosphate (4.00equivalents) are suspended under nitrogen atmosphere in DMSO and stirredat 120° C. until completion (usually 4 to 16 h). After chilling to roomtemperature, the reaction mixture is poured into water. The precipitatedcrude product is filtered off, washed with water and dissolved indichloromethane. The resulting solution is dried over MgSO₄, filteredand concentrated in vacuo. The crude product is purified byrecrystallization from an appropriate solvent (toluene, ethanol,n-hexane) or by flash chromatography. The product is obtained as asolid.

In particular, the donor molecule D-H is a 3,6-substituted carbazole(e.g., 3,6-dimethylcarbazole, 3,6-diphenylcarbazole,3,6-di-tert-butylcarbazole), a 2,7-substituted carbazole (e.g.,2,7-dimethylcarbazole, 2,7-diphenylcarbazole,2,7-di-tert-butylcarbazole), a 1,8-substituted carbazole (e.g.,1,8-dimethylcarbazole, 1,8-diphenylcarbazole,1,8-di-tert-butylcarbazole), a 1-substituted carbazole (e.g.,1-methylcarbazole, 1-phenylcarbazole, 1-tert-butylcarbazole), a2-substituted carbazole (e.g., 2-methylcarbazole, 2-phenylcarbazole,2-tert-butylcarbazole), or a 3-substituted carbazole (e.g.,3-methylcarbazole, 3-phenylcarbazole, 3-tert-butylcarbazole).

Exemplarily a halogen-substituted carbazole, particularly3-bromocarbazole, can be used as D-H.

In a subsequent reaction a boronic acid ester functional group orboronic acid functional group may be exemplarily introduced at theposition of the one or more halogen substituents, which was introducedvia D-H, to yield the corresponding carbazol-3-ylboronic acid ester orcarbazol-3-ylboronic acid, e.g., via the reaction withbis(pinacolato)diboron (CAS No. 73183-34-3). Subsequently, one or moresubstituents R^(a) may be introduced in place of the boronic acid estergroup or the boronic acid group via a coupling reaction with thecorresponding halogenated reactant R^(a)-Hal, preferably R^(a)—Cl andR^(a)—Br.

Alternatively, one or more substituents R^(a) may be introduced at theposition of the one or more halogen substituents, which was introducedvia D-H, via the reaction with a boronic acid of the substituent R^(a)[R^(a)—B(OH)₂] or a corresponding boronic acid ester.

HPLC-MS:

HPLC-MS spectroscopy is performed on a HPLC by Agilent (1100 series)with MS-detector (Thermo LTQ XL). A reverse phase column 4.6 mm×150 mm,particle size 5.0 μm from Waters (without pre-column) is used in theHPLC. The HPLC-MS measurements are performed at room temperature (rt)with the solvents acetonitrile, water and THF in the followingconcentrations:

solvent A: H₂O (90%) MeCN (10%) solvent B: H₂O (10%) MeCN (90%) solventC: THF (50%) MeCN (50%)

From a solution with a concentration of 0.5 mg/ml an injection volume of15 μL is taken for the measurements. The following gradient is used:

Flow rate [ml/min] time [min] A[%] B[%] C[%] 3 0 40 50 10 3 10 15 25 603 14 15 25 60 3 14.01 40 50 10 3 18 40 50 10 3 19 40 50 10

Ionisation of the probe is performed by APCI (atmospheric pressurechemical ionization).

Cyclic Voltammetry

Cyclic voltammograms are measured from solutions having concentration of10⁻³ mol/l of the organic molecules in dichloromethane or a suitablesolvent and a suitable supporting electrolyte (e.g. 0.1 mol/l oftetrabutylammonium hexafluorophosphate). The measurements are conductedat room temperature under nitrogen atmosphere with a three-electrodeassembly (Working and counter electrodes: Pt wire, reference electrode:Pt wire) and calibrated using FeCp₂/FeCp₂ ⁺ as internal standard. TheHOMO data was corrected using ferrocene as internal standard againstSCE.

Density Functional Theory Calculation

Molecular structures are optimized employing the BP86 functional and theresolution of identity approach (RI). Excitation energies are calculatedusing the (BP86) optimized structures employing Time-Dependent DFT(TD-DFT) methods. Orbital and excited state energies are calculated withthe B3LYP functional. Def2-SVP basis sets (and a m4-grid for numericalintegration are used. The Turbomole program package is used for allcalculations.

Photophysical Measurements

Sample pretreatment: Spin-coating

Apparatus: Spin150, SPS euro.

The sample concentration is 10 mg/ml, dissolved in a suitable solvent.

Program: 1) 3 s at 400 U/min; 20 s at 1000 U/min at 1000 Upm/s. 3) 10 sat 4000 U/min at 1000 Upm/s. After coating, the films are dried at 70°C. for 1 min.

Photoluminescence Spectroscopy and TCSPC (Time-Correlated Single-PhotonCounting)

Steady-state emission spectroscopy is measured by a Horiba Scientific,Modell FluoroMax-4 equipped with a 150 W Xenon-Arc lamp, excitation- andemissions monochromators and a Hamamatsu R928 photomultiplier and atime-correlated single-photon counting option. Emissions and excitationspectra are corrected using standard correction fits.

Excited state lifetimes are determined employing the same system usingthe TCSPC method with FM-2013 equipment and a Horiba Yvon TCSPC hub.

Excitation Sources:

NanoLED 370 (wavelength: 371 nm, puls duration: 1.1 ns)

NanoLED 290 (wavelength: 294 nm, puls duration: <1 ns)

SpectraLED 310 (wavelength: 314 nm)

SpectraLED 355 (wavelength: 355 nm).

Data analysis (exponential fit) is done using the software suiteDataStation and DAS6 analysis software. The fit is specified using thechi-squared-test.

Photoluminescence Quantum Yield Measurements

For photoluminescence quantum yield (PLQY) measurements an Absolute PLQuantum Yield Measurement C9920-03G system (Hamamatsu Photonics) isused. Quantum yields and CIE coordinates are determined using thesoftware U6039-05 version 3.6.0. Emission maxima are given in nm,quantum yields Φ in % and CIE coordinates as x,y values. PLQY isdetermined using the following protocol:

-   -   1) Quality assurance: Anthracene in ethanol (known        concentration) is used as reference    -   2) Excitation wavelength: the absorption maximum of the organic        molecule is determined and the molecule is excited using this        wavelength    -   3) Measurement        -   Quantum yields are measured for sample of solutions or films            under nitrogen atmosphere. The yield is calculated using the            equation:

$\Phi_{PL} = {\frac{n_{photon},{emited}}{n_{photon},{absorbed}} = \frac{\int{{\frac{\lambda}{hc}\left\lbrack {{{Int}_{emitted}^{sample}(\lambda)} - {{Int}_{absorbed}^{sample}(\lambda)}} \right\rbrack}d\; \lambda}}{\int{{\frac{\lambda}{hc}\left\lbrack {{{Int}_{emitted}^{reference}(\lambda)} - {{Int}_{absorbed}^{reference}(\lambda)}} \right\rbrack}d\; \lambda}}}$

-   -   -   wherein n_(photon) denotes the photon count and Int. the            intensity.

Production and Characterization of Organic Electroluminescence Devices

OLED devices comprising organic molecules according to the invention canbe produced via vacuum-deposition methods. If a layer contains more thanone compound, the weight-percentage of one or more compounds is given in%. The total weight-percentage values amount to 100%, thus if a value isnot given, the fraction of this compound equals to the differencebetween the given values and 100%.

The not fully optimized OLEDs are characterized using standard methodsand measuring electroluminescence spectra, the external quantumefficiency (in %) in dependency on the intensity, calculated using thelight detected by the photodiode, and the current. The OLED devicelifetime is extracted from the change of the luminance during operationat constant current density. The LT50 value corresponds to the time,where the measured luminance decreased to 50% of the initial luminance,analogously LT80 corresponds to the time point, at which the measuredluminance decreased to 80% of the initial luminance, LT 95 to the timepoint, at which the measured luminance decreased to 95% of the initialluminance etc. Accelerated lifetime measurements are performed (e.g.applying increased current densities). Exemplarily LT80 values at 500cd/m² are determined using the following equation:

${{LT}\; 80\left( {500\frac{{cd}^{2}}{m^{2}}} \right)} = {{LT}\; 80\left( L_{0} \right)\left( \frac{L_{0}}{500\frac{{cd}^{2}}{m^{2}}} \right)^{1.6}}$

wherein L₀ denotes the initial luminance at the applied current density.The values correspond to the average of several pixels (typically two toeight), the standard deviation between these pixels is given. Figuresshow the data series for one OLED pixel.

Example 1

Example 1 was synthesized according to AAV1 (86% yield) and AAV7 (88%yield).

MS (HPLC-MS), m/z (retention time): 801.7 (12.45 min).

FIG. 1 depicts the emission spectrum of example 1 (10% by weight inPMMA). The emission maximum is at 450 nm. The photoluminescence quantumyield (PLQY) is 83%, the full width at half maximum is 0.44 eV and theemission lifetime is 28 μs. The resulting CIE_(x) coordinate isdetermined at 0.16 and the CIE_(y) coordinate at 0.13.

Example 2

Example 2 was synthesized according to AAV1 (86% yield) and AAV7 (98%yield).

MS (HPLC-MS), m/z (retention time): 882.1 (10.80 min).

FIG. 2 depicts the emission spectrum of example 2 (10% by weight inPMMA). The emission maximum is at 462 nm. The photoluminescence quantumyield (PLQY) is 76%, the full width at half maximum is 0.45 eV and theemission lifetime is 10 μs. The resulting CIE_(x) coordinate isdetermined at 0.16 and the CIE_(y) coordinate at 0.18.

Example 3

Example 3 was synthesized similarly to AAV1 (52% yield), wherein4-Bromo-2,3-difluorobenzonitrile was used instead of4-Bromo-2,6-difluorobenzonitrile and AAV7 (35% yield).

MS (HPLC-MS), m/z (retention time): 881.3 (9.09 min).

FIG. 3 depicts the emission spectrum of example 3 (10% by weight inPMMA). The emission maximum is at 462 nm. The photoluminescence quantumyield (PLQY) is 73%, the full width at half maximum is 0.45 eV and theemission lifetime is 29 μs. The resulting CIE_(x) coordinate isdetermined at 0.16 and the CIE_(y) coordinate at 0.18.

Device D1

Example 2 was tested in an OLED-device D1 with the following layerstructure:

Schicht Dicke 8 100 nm Al 7 2 nm Liq 6 30 nm NBPhen 5 50 nm 2(10%):9-[3,5-bis(2- dibenzofuranyl)phenyl]-9H- carbazole (70%):T2T (20%)4 10 nm 9-[3,5-Bis(2- dibenzofuranyl)phenyl]-9H- carbazol 3 10 nm TCTA 2100 nm NPB 1 130 nm ITO Substrate Glass

For D1 an external quantum efficiency (EQE) at 1000 cd/m² of 8.3% wasdetermined. The emission maximum is at 475 nm and CIEy is 0.25 at 7 V.

Additional Examples of Organic Molecules of the Invention

FIGURES

FIG. 1 Emission spectrum of example 1 (10% by weight) in PMMA.

FIG. 2 Emission spectrum of example 2 (10% by weight) in PMMA.

FIG. 3 Emission spectrum of example 3 (10% by weight) in PMMA.

1. An organic molecule, comprising A first chemical moiety comprising orconsisting of a structure of formula I,

and Two second chemical moieties, each independently from anothercomprising or consisting of a structure of formula II,

wherein the first chemical moiety is linked to each of the two secondchemical moieties via a single bond; wherein T is the binding site of asingle bond linking the first chemical moiety to one of the two secondchemical moieties or is hydrogen; V is the binding site of a single bondlinking the first chemical moiety to one of the two second chemicalmoieties or is hydrogen; W is the binding site of a single bond linkingthe first chemical moiety to one of the two second chemical moieties oris selected from the group consisting of hydrogen, CN and CF₃; X is thebinding site of a single bond linking the first chemical moiety to oneof the two second chemical moieties or is selected from the groupconsisting of hydrogen, CN and CF₃; Y is the binding site of a singlebond linking the first chemical moiety to one of the two second chemicalmoieties or is selected from the group consisting of hydrogen, CN andCF₃; # represents the binding site of a single bond linking the firstchemical moiety to one of the two second chemical moieties; Z is at eachoccurrence independently from another selected from the group consistingof a direct bond, CR³R⁴, C═CR³R⁴, C═O, C═NR³, NR³, O, SiR³R⁴, S, S(O),and S(O)₂; R¹, R², R^(m) is independently from each other at eachoccurrence independently from another selected from the group consistingof hydrogen, deuterium, C₁-C₅-alkyl, wherein one or more hydrogen atomsare optionally substituted by deuterium; C₂-C₈-alkenyl, wherein one ormore hydrogen atoms are optionally substituted by deuterium;C₂-C₈-alkynyl, wherein one or more hydrogen atoms are optionallysubstituted by deuterium; and C₆-C₁₈-aryl, which is optionallysubstituted with one or more substituents R⁶; and R^(a), R³ and R⁴ is ateach occurrence independently from another selected from the groupconsisting of hydrogen, deuterium, N(R⁵)₂, OR⁵, Si(R⁵)₃, B(OR⁵)₂,OSO₂R⁵, CF₃, CN, F, Br, I, C₁-C₄₀-alkyl, which is optionally substitutedwith one or more substituents R⁵ and wherein one or more non-adjacentCH₂-groups are optionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂,Sn(R⁵)₂, C═O, C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₁-C₄₀-alkoxy, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₁-C₄₀-thioalkoxy, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₂-C₄₀-alkenyl, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₂-C₄₀-alkynyl, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵; C₆-C₆₀-aryl,which is optionally substituted with one or more substituents R⁵; andC₃-C₅₇-heteroaryl, which is optionally substituted with one or moresubstituents R⁵; R⁵ is at each occurrence independently from anotherselected from the group consisting of hydrogen, deuterium, N(R⁶)₂, OR⁶,Si(R⁶)₃, B(OR⁶)₂, OSO₂R⁶, CF₃, CN, F, Br, I, C₁-C₄₀-alkyl, which isoptionally substituted with one or more substituents R⁶ and wherein oneor more non-adjacent CH₂-groups are optionally substituted by R⁶C═CR⁶,C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O, C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO,SO₂, NR⁶, O, S or CONR⁶; C₁-C₄₀-alkoxy, which is optionally substitutedwith one or more substituents R⁶ and wherein one or more non-adjacentCH₂-groups are optionally substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂,Sn(R⁶)₂, C═O, C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;C₁-C₄₀-thioalkoxy, which is optionally substituted with one or moresubstituents R⁶ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;C₂-C₄₀-alkenyl, which is optionally substituted with one or moresubstituents R⁶ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;C₂-C₄₀-alkynyl, which is optionally substituted with one or moresubstituents R⁶ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶; C₆-C₆₀-aryl,which is optionally substituted with one or more substituents R⁶; andC₃-C₅₇-heteroaryl, which is optionally substituted with one or moresubstituents R⁶; R⁶ is at each occurrence independently from anotherselected from the group consisting of hydrogen, deuterium, OPh, CF₃, CN,F, C₁-C₅-alkyl, wherein one or more hydrogen atoms are optionally,independently from each other substituted by deuterium, CN, CF₃, or F;C₁-C₅-alkoxy, wherein one or more hydrogen atoms are optionally,independently from each other substituted by deuterium, CN, CF₃, or F;C₁-C₅-thioalkoxy, wherein one or more hydrogen atoms are optionally,independently from each other substituted by deuterium, CN, CF₃, or F;C₂-C₅-alkenyl, wherein one or more hydrogen atoms are optionally,independently from each other substituted by deuterium, CN, CF₃, or F;C₂-C₅-alkynyl, wherein one or more hydrogen atoms are optionally,independently from each other substituted by deuterium, CN, CF₃, or F;C₆-C₁₈-aryl, which is optionally substituted with one or moreC₁-C₅-alkyl substituents; C₃-C₁₇-heteroaryl, which is optionallysubstituted with one or more C₁-C₅-alkyl substituents; N(C₆-C₁₈-aryl)₂;N(C₃-C₁₇-heteroaryl)₂, and N(C₃-C₁₇-heteroaryl)(C₆-C₁₈-aryl); whereinthe substituents R^(a), R³, R⁴ or R⁵ independently from each otheroptionally form a mono- or polycyclic, aliphatic, aromatic and/orbenzo-fused ring system with one or more substituents R^(a), R³, R⁴ orR⁵; wherein exactly one substituent selected from the group consistingof W, X, and Y is CN or CF₃, and exactly two substituents selected fromthe group consisting of T, V, W, X and Y represent the binding sites ofa single bond linking the first chemical moiety and one of the twosecond chemical moieties.
 2. The organic molecule according to claim 1,wherein R¹, R² and R^(m) are at each occurrence independently fromanother selected from the group consisting of H, methyl and phenyl. 3.The organic molecule according to claim 1, wherein W is CN.
 4. Theorganic molecule according to claim 1, wherein the two second chemicalmoieties, each at each occurrence independently from another comprise astructure of formula IIa:


5. The organic molecule according to claim 4, wherein the two secondchemical moieties, each at each occurrence independently from anothercomprise a structure of formula IIb:

wherein R^(b) is at each occurrence independently from another selectedfrom the group consisting of deuterium, N(R⁵)₂, OR⁵, Si(R⁵)₃, B(OR⁵)₂,OSO₂R⁵, CF₃, CN, F, Br, I, C₁-C₄₀-alkyl, which is optionally substitutedwith one or more substituents R⁵ and wherein one or more non-adjacentCH₂-groups are optionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂,Sn(R⁵)₂, C═O, C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₁-C₄₀-alkoxy, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₁-C₄₀-thioalkoxy, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₂-C₄₀-alkenyl, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₂-C₄₀-alkynyl, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵; C₆-C₆₀-aryl,which is optionally substituted with one or more substituents R⁵; andC₃-C₅₇-heteroaryl, which is optionally substituted with one or moresubstituents R⁵; and wherein apart from that the definitions in claim 1apply.
 6. The organic molecule according to claim 4, wherein the twosecond chemical moieties, each at each occurrence independently fromanother comprise a structure of formula IIc:

wherein R^(b) is at each occurrence independently from another selectedfrom the group consisting of deuterium, N(R⁵)₂, OR⁵, Si(R⁵)₃, B(OR⁵)₂,OSO₂R⁵, CF₃, CN, F, Br, I, C₁-C₄₀-alkyl, which is optionally substitutedwith one or more substituents R⁵ and wherein one or more non-adjacentCH₂-groups are optionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂,Sn(R⁵)₂, C═O, C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₁-C₄₀-alkoxy, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₁-C₄₀-thioalkoxy, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₂-C₄₀-alkenyl, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₂-C₄₀-alkynyl, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵; C₆-C₆₀-aryl,which is optionally substituted with one or more substituents R⁵; andC₃-C₅₇-heteroaryl, which is optionally substituted with one or moresubstituents R⁵; and wherein apart from that the definitions in claim 1apply.
 7. The organic molecule according to claim 5, wherein R^(b) is ateach occurrence independently from another selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, Ph, which is optionallysubstituted with one or more substituents independently from each otherselected from the group consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃ andPh; pyridinyl, which is optionally substituted with one or moresubstituents independently from each other selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃ and Ph; pyrimidinyl, which isoptionally substituted with one or more substituents independently fromeach other selected from the group consisting of Me, ^(i)Pr, ^(t)Bu, CN,CF₃ and Ph; carbazolyl, which is optionally substituted with one or moresubstituents independently from each other selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃ and Ph; triazinyl, which isoptionally substituted with one or more substituents independently fromeach other selected from the group consisting of Me, ^(i)Pr, ^(t)Bu, CN,CF₃, and Ph; and N(Ph)₂.
 8. The organic molecule according to claim 6,wherein R^(b) is at each occurrence independently from another selectedfrom the group consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, Ph, which isoptionally substituted with one or more substituents independently fromeach other selected from the group consisting of Me, ^(i)Pr, ^(t)Bu, CN,CF₃ and Ph; pyridinyl, which is optionally substituted with one or moresubstituents independently from each other selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃ and Ph; pyrimidinyl, which isoptionally substituted with one or more substituents independently fromeach other selected from the group consisting of Me, ^(i)Pr, ^(t)Bu, CN,CF₃ and Ph; carbazolyl, which is optionally substituted with one or moresubstituents independently from each other selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃ and Ph; triazinyl, which isoptionally substituted with one or more substituents independently fromeach other selected from the group consisting of Me, ^(i)Pr, ^(t)Bu, CN,CF₃, and Ph; and N(Ph)₂.
 9. A process for preparing organic moleculesaccording to claim 1, wherein a2-trifluormethyl-3-R¹-5-R¹-4-R²-6-R^(m)-phenylboronic acid is used as areactant.
 10. An optoelectronic device comprising at least one of aluminescent emitter and/or a host material, electron transport material,hole injection material and hole blocking material, the electrontransport material, the hole injection material and the hole blockingmaterial comprising the organic molecule according to claim
 1. 11. Theoptoelectronic device according to claim 10, wherein the optoelectronicdevice is selected from the group consisting of an organiclight-emitting diode (OLEDS), a light-emitting electrochemical cell, anOLED-sensors, an organic diode, an organic solar cell, an organictransistor, an organic field-effect transistor, an organic laser, and adown-conversion element.
 12. A composition comprising: (a) at least oneorganic molecule according to claim 1, in particular in the form of anemitter and/or a host, and (b) one or more emitter and/or hostmaterials, which differ from the organic molecule of claims 1, and (c)optionally, one or more dyes and/or one or more solvents.
 13. Anoptoelectronic device, comprising one organic molecule according toclaim 1 or a composition according to claim 12, in particular in form ofa device selected from the group consisting of organic light-emittingdiode (OLED), light-emitting electrochemical cell OLED-sensor, organicdiode, organic solar cell, organic transistor, organic field-effecttransistor, organic laser and down-conversion element.
 14. Theoptoelectronic device according to claim 13, comprising a substrate, ananode and a cathode, wherein the anode or the cathode are disposed onthe substrate and at least a light-emitting layer, which is arrangedbetween the anode and the cathode and which comprises the organicmolecule according to claim 1 or a composition according to claim 12.15. A process for producing an optoelectronic device, wherein an organicmolecule according to claim 1 or a composition according to claim 12 isused, in particular comprising the processing of the organic compound byvacuum evaporation method or from a solution.